Dimethylformamide → Methyl 3-{6-[bis(4-methoxyphenyl)phenylmethoxy]hexanoyl}pyrrolo[4,5-e]indoline-7-carboxylate

HRID 130601ノート

反応式

HRID 130601 の反応式
C1[C:5]2=[C:6]3[C:10](=[CH:11]C=C2NC=1)[NH:9][CH:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:7]3.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:26][CH:27](CC)[CH2:28][CH2:29][C:30](OC2C=CC([N+]([O-])=O)=CC=2)=O)=[CH:21][CH:20]=1.[CH2:58]([N:60]([CH2:63][CH3:64])[CH2:61][CH3:62])[CH3:59].CN(C=[O:69])C>>[CH3:57][O:56][C:53]1[CH:52]=[CH:51][C:50]([C:25]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:59][C:58]([N:60]2[C:63]3[C:5](=[C:6]4[C:10](=[CH:11][CH:64]=3)[NH:9][CH:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:7]4)[CH:62]=[CH:61]2)=[O:69])=[CH:55][CH:54]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66717311Methyl pyrrolo[4,5-e]indoline-7-carboxylateHCID 686370484-Nitrophenyl 4-[bis(4-methoxyphenyl)phenylmethoxy]hexanoate

生成物 1

HCID 69198674Methyl 3-{6-[bis(4-methoxyphenyl)phenylmethoxy]hexanoyl}pyrrolo[4,5-e]indoline-7-carboxylate

実験手順

A solution of methyl pyrrolo[4,5-e]indoline-7-carboxylate (2.7 g, 12.5 mmol) prepared according to Boger et al (J. Org. Chem. 52:1521 (1987)), 4-nitrophenyl 4-[bis(4-methoxyphenyl)phenylmethoxy]hexanoate (6.9 g, 12.5 mmol) and triethylamine (2 mL) in 50 mL of anhydrous DMF was stirred at room temperature for 5 h and then concentrated. The resulting oil was left at room temperature overnight (˜15 h). The oil was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic phase was washed twice with diluted sodium bicarbonate, saturated sodium chloride and dried over sodium sulfate. The crude product obtained after removal of the solvent was crystallized from ethyl acetate. The yield of the crystalline product 15 was 5.9 g (75%). 1H NMR (DMSO-d6) δ 11.94 (s, 1H), 8.24 (d, J=9 Hz, 1H), 7.4-7.2 (m, 10H), 7.07 (s, 1H), 6.87 (d, J=9 Hz, 4H), 4.16 (t, J=8 Hz, 2H), 3.87 (s, 3H), 3.72 (s, 6H), 3.28 (t, J=8 Hz, 2H), 2.96 (t, J=6 Hz, 2H), 2.42 (t, J=7 Hz, 2H), 1.58 (m, 4H), 1.41 (m, 2H).

後処理

  1. concentrationconcentrated
  2. waitThe resulting oil was left at room temperature overnight (˜15 h)
  3. customThe oil was partitioned between ethyl acetate and 5% sodium bicarbonate
  4. washThe organic phase was washed twice with diluted sodium bicarbonate, saturated sodium chloride
  5. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-f0ca08afb0594af0ac53aaeb398245be
出典データセット
uspto-grants-2008_06
特許番号
US07381818B2

反応ノート

読み込み中…